Home Vacation Rentals By Owner In Sarasota, FL

Showing 2420 Of 3494 Vacation Rentals
Slider Thumb
Exceptional(23)

$193.47

/ Nightly
Cottage

Book Me Baby! Pool, Pet-Friendly Paradise Near Downtown Sarasota

Sarasota, Florida, United States

Pinkie Flamingo Welcomes You To Hazel's Hideaway!brbrThree month (90 Day) Min For Season. Just nine blocks from Sarasota's bustling Main Street, cottage guests can enjoy a private and serene poolside setting and a 30-foot lap pool in an historic neighborhood. This cute one-bedroom bungalow has a separate king bedroom, full bath, kitchenette and living room. Less than two blocks away is Gillespie Park, with tennis courts, basketball courts, dog park, pond and gazebo. This charming pet-friendly retreat is actually a detached guest house set on a quiet, private gated corner lot on the edge of The Rosemary District and Gillespie Park. Dogs and cats welcome! Pets are people too:) brbrCome To Florida...For The Fun of It!brbrAll of Pinkie's Properties Have A Few Things In Commonbr• Must Be 25 To Bookbr• No Smoking br• Cancellation OK 30 Days Prior To Check-Inbr• Sheets & Bath Towels Included…BYO Beach Towelsbr• All Kitchens Fully-Equipped With Cooking/Eating Utensils… BYO Spices & Foodbr• Basic Essentials Starter Set Only…TP, Paper Towels, Trash Bags, Soaps, Etc …Depending on Length of Stay You May Need More
Bed 1

Bed

Bath 1

Bath

Sleep 6

Sleeps
Slider Thumb

$259.9

/ Nightly
Condo

Luxury Tennis Retreat Near Siesta Key, Bath and Racquet Club. Sleeps 4.

Sarasota, Florida, United States

Welcome to Bath & Racquet Club, a newly reimagined Sarasota destination built around sport, wellness, and clean design. This one bedroom, one bathroom residence is purpose built for 1 week stays or more, comfortably sleeping four with a private bedroom and a quality pullout sofa in the living area.brbrThe unit is new construction and finished to a high standard. Expect a bright, open layout with a fully equipped kitchen, modern bath, and thoughtful storage so you can settle in for a weekend or a longer stay. The bedroom offers a quiet retreat with a comfortable bed and premium linens. The living area is set up for both relaxation and flexible sleeping. Fast WiFi supports remote work. Smart TV is ready for your accounts.brbrLocation is practical and easy. You are within a short drive of Siesta Key Beach, downtown Sarasota, and the best dining and shopping in the area. Parking is simple. Access is smooth with self-check in.brbrWhat sets this property apart is the setting. Bath & Racquet Club is a revived landmark centered on racquet sports and an active lifestyle. You are not just renting a condo. You are staying inside a private club environment designed for people who want to move, play, and unwind.brbr**Amenities**brbr**In Residence**brbr* 1 bedroom, 1 bathroom, sleeps 4br* King or queen bed in bedroom, pullout sofa in living roombr* Fully equipped kitchen with cookware, dishes, coffee makerbr* Modern bathroom with fresh towels and essentialsbr* Fast WiFi for work and streamingbr* Smart TVbr* In unit climate controlbr* Washer and dryer access in unitbr* Clean, contemporary finishes throughoutbrbr**Optional Club Access at Bath & Racquet**brbr* Multiple Indoor and outdoor tennis, pickle ball, Padel ball courts in a private club settingbr* Racquet sport programming and events (as scheduled)br* Landscaped grounds designed for walking and relaxationbr* On site social spaces for guests and membersbrbr**Location Highlights**brbr* Short drive to Siesta Key Beachbr* Close to downtown Sarasota dining, arts, and nightlifebr* Easy access to grocery stores and daily essentials. br* Trader Joe's and Restaurants within walking distancebr* Central location for exploring Sarasota and the Gulf Coastbrbr**Guest Experience**brbrThis is a simple, high-quality stay. You arrive, settle in quickly, and have access to a unique sports focused environment that is rare in this market. Spend your morning on court, your afternoon at the beach, and your evening in town. The layout works for couples, small families, or two guests traveling together.brbrIf you are coming for tennis or pickleball, you will appreciate the convenience of staying on site. If you are coming for the beach and dining, you will appreciate how close everything is without the congestion of beachfront properties.brbr**Good to Know**brbr* Non smoking unitbr* No parties or eventsbr* Quiet hours respectedbr* Club access may vary based on programming or membership structurebrbrThis is a new offering with limited availability. Book early to secure your dates at Bath & Racquet Club.
Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
Slider Thumb
Exceptional(25)

$294.71

/ Nightly
Condo

New to Rental market Luxury remodeled condo located directly on Siesta Key Beach

Sarasota, Florida, United States

Located directly on the beautiful white quartz sands of Siesta Key Beach, this gorgeous 2 bedroom, 2 bath remodeled condo completed in November 2024 offers a master with brand new King size Bed and ensuite bath including glass enclosed shower; Bedroom 2 offers 2 brand new Queen size beds with adjacent full main bath with tub/shower combo. Property offers 2 heated pools, beach chairs and covered parking for one car
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
Slider Thumb

$214.65

/ Nightly
Apartment

2BR Beachy Speakeasy In St Armand's w/ Rooftop Deck. Walk to Lido Beach

Sarasota, Florida, United States

NOW BOOKING SUMMER 2026 GETAWAYS! Step into your holiday now at a Sarasota paradise nestled in the heart of St Armand's Circle! This isn't just any rental, it's an experience waiting to unfold! brbr*Please note our Strict Cancellation Policy listed only applies to bookings during high season from January through April. See our Custom Seasonal Cancellation Policy at the bottom of this description and in our Rental Agreement.brbrPicture this: A Beach Vacation Getaway in a hidden, 1-of-a-kind apartment with a Beachy Speakeasy Vibe that is located on the rooftop of a retail store. It features a rooftop deck, outdoor dining under a gazebo with string lights, with a lounge area complete with cushioned lounge chairs, a single daybed, a double daybed with clamshell canopy, and a retro vintage umbrella. Plus, it's a 5min walk to the pristine sands of Lido Beach, and surrounded by the charm of boutiques, and eateries within walking distance!brbrWelcome to the Beachy Speakeasy! Thanks for checking us out! Whether you are looking to stay a few days, a week, or a month, we are happy to host you! Stays of 28 days or more GET A 35% DISCOUNT! brbrYour adventure starts the moment you step through that unassuming door, greeted by a hidden washer and dryer, a ocean-blue concrete-floor corridor with vibrant blue walls, leading to a small 2 flight stairway (no elevators here!), and a code-locked doorknob entrance to your abode on the second floor for extra security and privacy..brbrInside, discover a newly updated and upgraded, thoughtfully designed 2-bedroom, 1-bath haven with a fully equipped kitchen. The fusion of beachy elements and speakeasy accents is evident in every nook and cranny.brbrParking: While a dedicated parking space isn't available, if you have a car to park, there are plenty of nearby free and paid street parking spots very close by within walking distance (150-200ft from the door). Parking will not be an issue no matter what time of year you book. The Beachy Speakeasy is a haven for pedestrians and Uber aficionados. Want to bike around Not only can you can rent electric scooters and bikes nearby next to St Armand's Market on Monroe Dr, or use electric scooter rentals available around the Circle in different locations that have an app to rent from, but we are now about to offer our own electric scooter and e-bike amenities! Details & Pictures Coming Very Soon!brbrWe provide the beach gear: Chairs, beach umbrella, ice chest, and even a trusty beach wagon so you can walk to the beach for a hassle-free time at the shore without the parking fuss.brbrExplore the area with ease - the a free trolley whisks you from St Armand's Circle to Downtown Sarasota and beyond.brbrBack at your cozy retreat, the unit has been updated in 2026 with new paint throughout, new furniture additions, new bedding, linens and towels and even more upgrades! Lounge in the main living area with a comfortable brand new blue linen pull-out sleeper sofa, 2 blue velvet chairs, a coffee table with 2 pop-up tables for laptops or to enjoy a meal while watching streaming TV and coastal-themed accents. Head out to the rooftop deck for morning coffee and breakfast, lunch, or dinner & evening drinks on our new patio dining table with 4 chairs under the gazebo with string lights! You can also enjoy sun-soaked relaxation, rooftop yoga (mats provided!), or even a small workout with free weights. We have our rooftop garden lounge area directly off the wooden deck that features 2 lounge chairs with new cushions, a daybed with a new vintage retro umbrella, and a side table that has a hidden ice chest inside for soaking up the sun. The rooftop garden lounge area is surrounded by 4 tropical plants, including areca palms, a pigmy palm and a hibiscus plant that is constantly blooming our favorite red hibiscus flowers and it all sits on top of a perfectly manicured rooftop AstroTurf lawn. Enjoy another sitting area with AstroTurf lawn that has 2 Adirondack chairs and new queen sized daybed with cushions and clamshell canopy!brbrReady for a restful slumber The primary bedroom, the Tortuga Morada Suite (Purple Turtle Suite) has a Beachy vibe and boasts a luxurious memory foam queen bed, hotel style sheets, new beachy comforters, 4 new pillows, 2 extra seating areas including a blue velvet futon sofa with a rolling laptop desk, a smart streaming tv, smart speaker, sound machine, dehumidifier, wireless chargers and usb ports for corded charging of your electronic devices, alarm clocks, luggage racks, and a dresser with LED lights and a charging station. There are even robes available for your use. brbrThe second bedroom, the Pineapple Room, has a Speakeasy vibe, and is newly painted and designed, offers equal comfort without a window, perfect for those serene sleep-ins. It also features a mirrored wall, pineapple lamps and decor, a remote controlled crystal fandalier, smart tv, smart speaker, luggage rack, dresser and clothing rack with robes. A sound machine is also included on the champagne gold nightstands. Both bedrooms have all new high end memory foam mattress toppers, bedding and pillows.brbrHungry or in need of a caffeine fix The well-equipped kitchen has you covered with a drip coffee pot, Vertuo Nespresso machine (with frother), and all the essentials to whip up a meal or a delightful brew.brbrNeed to catch up on work A dedicated workspace equipped with a chair, laptop desk and a printer/scanner is at your service. A new computer is being installed as well.brbrThe bathroom Small, but very adequate, with a walk-in shower featuring newly installed, Life Proof, non-slip Carrera marble-like ceramic mosaic tile floor and single spacious vanity! Stocked with shampoo, conditioner, and soap, hairdryer, flatiron, and more because we've got your back, even if you forget the essentials!brbrSo come, dive into the Beachy Speakeasy experience -it's not just a rental, it's a lifestyle waiting to be embraced!brbr**If an early check-in is wanted, inquire with us to see if we can accommodate you. If there are no same-day guests check-outs, we may be able to arrange early check-in for an additional tiered fee depending on how many hours earlier the check-in is. The same applies for a Late checkout. If you need a guaranteed early check-in or check-out, please book the day before or after so it will stay guaranteedbrbr**We can sometimes accommodate early baggage drop-off for a $50 fee or you can utilize local baggage storage (inquire for details and we can send a link to you)brbr**Baby and kids items are available for rental with delivery and pick-up - Inquire with us!brbr**Regarding Location & Entry** : It's true, our front door resides in an unexpected locale between dumpsters and trash cans from neighboring retail stores and restaurants (see photos). Our entrance is located on the rear side of the building. We're drawing inspiration from hidden speakeasies, bringing a touch of adventure to your stay. Rest assured, you are in a safe & well lit area and in a nice neighborhood. We strive for transparency so you know exactly what to expect before stepping foot in this vibrant retreat!brbr***In regards to Florida's natural wildlife, floral and fauna, we will sometimes experience mosquitoes, ants, spiders, cockroaches, etc. outside. We have regular pest treatments performed both inside & outside the units. We also personally, utilize bait, traps and sprays to keep these insects outside where they belong. Please don't keep windows without screens or doors open too long as you nay inadvertently let some inside. Should you come across any pests during your stay, please make us aware so we can address the situation. While it's rare to come across these pests inside, a refund will not be offered for the occasional occurrence. We always want you to be comfortable during your stay and you will find that we act quickly and with compassion to resolve any issues you have. We just need to be aware of it in order to resolve anything. ***brbrI am also a licensed Realtor with a team at Berkshire Hathaway HomeServices, so feel free to reach out if you are looking to buy in the area. I'm always happy to help.brbrThere is NO POOL on the property but there is a public pool located on Lido Beach for a small daily feebrbrImportant: Before you arrive you will be asked to complete guest verification through third-party provider Truvi. This is done to ensure we are keeping up-to-date with short-term rental regulations as well as providing both our guests and our properties with extra protection. Truvi will contact you via email and/or text to complete the verification. Please do so prior to arriving at the property to enable a quick and easy check-in process. You will also be given the choice between a security deposit or a non-refundable damage waiver. There is also a separate rental agreement that is sent for e-signing.brbrOur custom seasonal cancellation policy and our refund policy:brJanuary - April : Strict - *Partial refund 60 days before check-in; No refund after 60 days before check-in.brMay-October: Moderate: *Partial refund 30 days before check-in; 50% refund 14-30 days before check-in. No refund after 14 days before check-in.brNovember - December: Firm - *Partial refund 60 days before check-in; 50% refund 30-60 days before check-in. No refund after 30 days before check-in.br*Partial refunds are further defined as 100% refunds minus processing fees incurred by the merchant - StripebrThe Host recommends that all guests obtain appropriate travel and personal insurance coverage to cover these charges in case of a cancellation.
Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(58)

$251.58

/ Nightly
Condo

Bay to Beach Condo with a Cabana Full of Beach gear.

Sarasota, Florida, United States

This beautifully furnished 2 bedroom, 2 bathroom unit provides you with a stunning view of the Sarasota Bay adorned with draping trees that hide multiple varieties of birds. The lanai is in a Key West theme with 2 chaise lounges looking out at the water and a bistro set for morning breakfast. brbrThe condo has a king size bed in the master bedroom, a newly renovated master bathroom, 1 full size bed and 1 twin size bed in the second bedroom, and a full size 2nd bath with tub/shower. There is also a full size inflatable mattress with sheets. Included are 2 flat screen TVs, free Wifi, use of 2 bicycles, linens, towels, a hairdryer, and an iron board and iron. The kitchen includes all the items you could possibly think of including a microwave, dish washer, full size refrigerator, coffee maker, etc. Additionally there are summer reading books and start up materials such as paper towels, toilet paper, detergent, etc. All we ask is that you replace what you use. There is a laundry unit steps from the unit next to the elevator. brbrThe amenities at Bay Tree club are plentiful. There are 2 piers that have benches you can sit on in the morning with your coffee and watch the sun rise or just enjoy some bay fishing. If you are lucky you may catch a glimpse of a manatee or a dolphin. There is a kayak launch if you decide to rent a kayak to visit the bird sanctuaries that surround the bay. Right downstairs from the condo is one of 2 heated pools. A few steps more will lead you to the picnic area that has gas grills and a beautiful view of the Sarasota Bay. brbrDirectly across the street is Turtle Beach. You have direct access to the condo's private cabana which includes umbrellas, chairs, a beach wagon, toys, and floats. There is also a 2nd heated pool, another picnic area, gas grills, bathrooms, and an outdoor fresh water shower. brbrThere are 3 restaurants in walking distance, the world famous Siesta Beach is about 4 miles north and downtown Sarasota hosts wonderful shopping, restaurants, theater, and so much more. Tampa Busch Gardens is a little more than 1 hour away and Orlando is a 2 hour drive. The condo will have a information on attractions that may be of interest.brbrI have been coming to Siesta Key for over 15 years. There is simply no place like it. You can enjoy the calm tranquil south end or take a quick ride, by car or the free trolley that stops directly in front of the condo, to Siesta Key Village for a little more of a bustling crowd. brbrIf you are adventurous, there are enough activities for the whole family. There are multiple places to rent kayaks, paddle boards, and jet skis. You can go parasailing, play golf, miniature golf, and even enjoy a movie. brbrSome of my favorite attractions include Mote Marine Aquarium, St. Armand's Circle and downtown Sarasota for one of a kind shopping and excellent restaurants. The Marie Shelby Botanical Garden is a lovely surprise of hidden beauty. Myakka State Park also offers a great opportunity to see more of Florida's wildlife. brbrBay Tree Club is a friendly community of repeat visitors who come year after year. Please reach out for more information. On parle francais. Hablamos espanol.
Bed 2

Bed

Bath 2

Bath

Sleep 5

Sleeps
Slider Thumb
Exceptional(13)

$116.9

/ Nightly
Condo

Awesome views, comfortable 2 Br plus Den w/sofabed condo

Sarasota, Florida, United States

Outstanding views of the Palm Aire Championship Golf Course and Waterway from this second floor Condo. 2 King Size Bedrooms , 2 Full Bathrooms plus a 3rd BR/Den w/ sleeper sofa and 55 in. Smart TV. Free cable TV & internet . The condo is clean, comfortable and completely furnished for your convenience including kitchen ware, microwave, coffee maker, towels, sheets, games, even beach chairs, toys and beach umbrella. Full size Washer and Dryer in unit. Just a short walk to either of the 2 beautiful heated pools. Parking right out front. Conveniently located close to shopping, UTC Mall, beaches, golfing, baseball fields, airport, boating, restaurants and bars. Palm Aire has two beautiful and challenging 18-hole championship golf courses, Palm Aire offers Seasonal & Non-Resident Memberships for golf, as well as tennis or social memberships. Short drive to Lido Beach and a little further to Siesta Key or Bradenton Beach. Besides the beaches check out the museums, concerts, shows and local events. Sarasota is home to Spring training for the Baltimore Orioles baseball team in Sarasota or the Pittsburgh Pirates in Bradenton. Minutes from Ringling Museum, St. Armand's Circle, Mote Aquarium and Sarasota Jungle Gardens. Great Day trips to Tampas' Busch Gardens, Ellenton Outlets or Myakka River State Park, one of the oldest & largest Fl state parks, it has one of the state´s most diverse natural areas, where you'll find bicycle rentals, boat rides, lots of gator & Bird viewing, a canopy walk, playground and picnic areas. Palm Aire is just off the University Parkway exit of 75 with the new Nathan Benderson Park and High End UTC Mall and outlet stores, tons of shopping and dining options. 10 minutes to Sarasota Airport, 1 hour to Tampa Airport. There is an 12 % tourist tax in addition to the rent. Sorry NO PETS, NO TRUCKS, NO SMOKING.
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(13)

$294.6

/ Nightly
Condo

Piece of Heaven on Siesta Key

Sarasota, Florida, United States

Come stay at our lovely 2 bedroom, 2 bathroom condo on Siesta Key with access to the beach and the bay. Our unit is located on the bay side overlooking Sarasota Bay and is only a 3 minute walk to our private beach across the street. We have docks available to fish off of and to accommodate a boat if you decide to bring your boat or rent one while you are here. There are elevators and coin operated washers and dryers on each floor of the building. We are in close proximity to restaurants and shopping. There is a free trolley that can take you anywhere you want to go on Siesta Key that runs 7 days a week.brbrCome see for yourself why so many people return to Bay Tree Club year after year.
Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps
Slider Thumb
Exceptional(64)

$559.29

/ Nightly
Private Vacation Home

❤️ Charming Coastal Pool Home - 1 Mile to Siesta Key - Relax & Unwind

Sarasota, Florida, United States

Your Sarasota Sanctuary AwaitsbrbrWelcome to your private coastal retreat. This beautifully refurbished 3-bedroom, 2-bath pool home is ideally located just minutes from Siesta Key Beach, fine dining, and charming boutiques.brbrDesigned with comfort and elegance in mind, the home features curated designer furnishings, a fully equipped gourmet kitchen, and light-filled open living spaces that invite relaxation.brbrStep outside to your own private oasis. Enjoy the heated pool, with a baby safety fence available upon request, surrounded by a serene setting perfect for unwinding after a day at the beach.brbrThe home comfortably accommodates up to 8 guests with premium hypoallergenic bedding, including a king suite, queen bedroom, full bedroom, and an additional high-quality airbed.brbrSituated in a peaceful, quiet neighborhood, this property is ideal for guests seeking a refined and relaxing getaway.brbrThis is a non-smoking, no-party home. We are not pet friendly. If you wish to request an exception for one dog, prior written approval is required before booking.brbrParking available for up to 3 vehicles.brbrExperience Sarasota living at its finest.
Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
Slider Thumb

$327.7

/ Nightly
Private Vacation Home

Spacious 4bed/2bath home in Sarasota w/pool 5 miles from Siesta Key Beach!

Sarasota, Florida, United States

Bring the whole family to this spacious coastal retreat, thoughtfully designed for your most ultimate relaxing stay! This home is ideal for large families, friend groups and snowbirds ready to spend their perfect vacation in South Sarasota.brbrDetails:brRooms to relax and recharge br-4 spacious bedrooms (1 king, 2 queens, 2 twins and a pullout sofa bed) smart tv’s included in each room.br- Includes closet space and dressers.brFully equipped kitchen and dining roombr- Full size kitchen with all major appliances, stocked with dish-ware, cookware, utensils, coffee maker and more!brConvenient bathroomsbr-2 full bathrooms supplied with towels, toiletries and a hairdryer.br Living and entertainment areasbr-2 separate living areas for quality time with family including smart tv’s, board games, books, decks of cards.br-Comfortable seating, 1 sofa bed, 2 couches. br- Extra blankets can be found in the ottoman near the couch in the main living room.brPrivate outdoor areabr-Fenced in backyard filled with beautiful plant life.br-Large private pool, fun for kids to splash around and relaxation for adults!br- Outdoor lounge area near the pool, perfect for soaking up the sun after a refreshing dip in the pool.brTropical screened in patiobr-Includes outdoor dining table and seating for everyone, perfect for early morning coffee or late night conversation and card games.br- Overlooks the pool. brBeach gear and Pool toysbr-Wagon, cooler, umbrella, beach chairs, pool floaties, towels, light up toys and goggles are supplied conveniently by the pool and in the garage. brLocationbr-Only 5 miles away from Siesta Key, the #1 beach in America!br-Located near grocery stores and high rated restaurants and shops.br-Family-friendly, inviting neighborhood.
Bed 4

Bed

Bath 2

Bath

Sleep 10

Sleeps
Slider Thumb
Exceptional(37)

$175.09

/ Nightly
Private Vacation Home

Charming Sarasota Home • Near Beaches & Downtown, 3bed, 2 bath.

Sarasota, Florida, United States

This house has everything you need for your vacation. A live oak canopy gives a tree house feel throughout this charming and centrally located home on the beautiful Cultural Coast of Florida. Minutes from downtown and each of Lido and Siesta Keys, you can access world class beaches, the heart of the theater and arts district, fine dining and the lifestyle that put Sarasota on the map. The three bedrooms are beautifully appointed with the a master queen, the second bedroom with two twin beds and additional bedroom with a queen.brbrThe fully appointed kitchen, separate dining room, bonus room with a pull out couch, two full baths, laundry facilities make this home a great retreat for a getaway or an extended stay.brbrWe look forward to your visit to Sarasota.brCertificate Number – The certificate number [VR24-00084]
Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
Slider Thumb
Exceptional(50)

$240.4

/ Nightly
Condo

2bed 2 bath sleeps 5 .. 3 smart TVs.. fully refurbished Very Close to the beach

Sarasota, Florida, United States

RENOVATED 2025 2 BED, 2 BATH CONDO 1st floor parking right outside WI-FI and smart tvsbr Sleeps 5brbrLounge 65 Samsung smart Flatscreen TV / L Shaped leather sofa, Glass top dining Table, Driftwood laminate flooring brbrMain Bedroom :55”samsung smart TV / King Pillow-top luxury Bed, Driftwood laminate flooringbrbrGuest Bedroom 55inch Wall-mounted samsung Flatscreen TV / Queen Memory-foam bed, Driftwood laminate flooring. brbrThis is our home away from home, so is completely equipped with everything you should need : luxury Bedding, Towels, Beach Towels, hair dryers in both bedrooms. Walk in closets with plenty of hanging storage, laundry baskets, beach cart umbrella , cooler , kids buckets and spadesbrbrWe have new (2025) equipped kitchen appliances new 2025 including keurig coffee machine. Electric kettle,toaster dishwasher, microwave, ceramic Hob, fridge freezer.brThere is a shared washing machine & tumble dryer just outside the door. brbrThere is a communal heated Pool, clubhouse that has a library of books to share,
Bed 2

Bed

Bath 2

Bath

Sleep 5

Sleeps
Slider Thumb
Exceptional(45)

$162.01

/ Nightly
Private Vacation Home

Sunny Sarasota Retreat • Steps to Siesta Key Bridge

Sarasota, Florida, United States

Charming updated west of trail home. Close to beaches, shopping, hospital, restaurants and world-class fishing. Walk to Sarasota Bay. Ride your bike to the beach. Granite kitchen counters. Tile and hardwood floors. Spacious and bright Florida room, terrace with room for BBQ, private back yard. Bring your family invite your friends. brbrThe two bedrooms are beautifully appointed with the a master queen, the second bedroom with two twin beds. brbrThe fully appointed kitchen, separate dining room, two full baths, laundry facilities make this home a great retreat for a getaway or an extended stay.brbrWe look forward to your visit to Sarasota. Certificate Number – The certificate number [VR24-00082]
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(11)

$738.77

/ Nightly
Condo

Stunning Condo with Ocean View and pool access on Siesta Key!

Sarasota, Florida, United States

Beach House Residence – a luxurious place to unwind for your unforgettable vacation! This stunning home offers an open floorplan, 4 Bedrooms, 3 bathrooms, with room for 10 guests. Enjoy beautiful views of the gulf and take in those gorgeous sunsets from the large, wrapping balcony. Venture on a stroll to the communities beach access or relax at the Calini Beach Club pool where you can get lounge chairs for enjoying the peaceful tropic breeze. With 13 public beach access points, wonderful shops and restaurants, Siesta Key promises great experiences for everyone who visits. Take advantage of the tranquil waters, soft sand, and warm sun as you explore all the island has to offer and unwind at the end of a fantastic day in this beautiful home. brbrBedding and Televisions:brBedroom 1 - King, TVbrBedroom 2 - King, TVbrBedroom 3 - KingbrBedroom 4 - 2 bunk beds (4 twins)brLiving Room - TVbrbrAdded Amenities Included in Your Stay:brComplimentary Bicycles,brWifi,brParking,brBeach Chairs,brBeach Towels,brBeach Wagon,brBeach Cooler,brPartner Property Pool Access,brAccess to Siesta Beach Pickleball Courts,brFree-Rides Around Siesta Key,brA 7-day week, Beachside Management office for your convenience and guest needs!br*Security authorization Hold taken upon check-in. Amount: $1,500
Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps
Slider Thumb
Exceptional(2)

$92.82

/ Nightly
Mobile Home

Private Cozy RV with AC and WiFi in Welcoming Sarasota.

Sarasota, Florida, United States

Your cozy getaway awaits in Sarasota at this recreational vehicle. This wonderful RV features 1 soothing queen bed, a shower in the bathroom, and essential amenities like heating, AC, and WiFi. Guests can enjoy the fitness area during their stay. Experience the magic of Sarasota at our recreational vehicle. Easy parking and private outdoor area.
Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
Slider Thumb
Exceptional(7)

$282.5

/ Nightly
Private Vacation Home

NEW! Artsy 3BR/2BA Pool Home Arlington Park Near Beaches

Sarasota, Florida, United States

Escape to Your Private Sarasota Oasis! brLooking for the perfect beach getaway Just a short drive from the world-famous Siesta Key and vibrant downtown Sarasota, this beautifully renovated 3BR/2BA pool home is your ideal home base in paradise!brbr★ Living AreabrThe bright and airy living room is designed for gathering and comfort. Sink into plush seating, enjoy smart TV streaming, and take advantage of the open flow to the kitchen and dining areas. Large windows and updated lighting create a warm, welcoming space.brThis home blends mid-century charm with modern updates. Recently renovated, it features sleek finishes, open-concept living spaces, and a coastal-chic aesthetic designed for relaxation and entertaining. Perfect for guests seeking both comfort and style during their Sarasota getaway.brbr★ KitchenbrA modern chef’s kitchen with granite countertops, stainless steel appliances, and a large island with bar seating. Fully stocked with cookware, dishes, and utensils—ideal for making anything from quick breakfasts to full family dinners.brbr★ DiningbrEnjoy meals together on the dining table for 6 guests, conveniently positioned between the kitchen and living room. The kitchen island also serves as a casual dining space or morning coffee bar for 4 guests. brbr★ BedroomsbrPrimary Suite: King bed, walk-in closet, en-suite bathroom with double vanity and walk-in shower. brGuest Bedroom 1: Queen bed, bright and cozy with a desk and chest of drawers.brGuest Bedroom 2: Queen bed, modern decoration with a desk. brEach bedroom is thoughtfully decorated with soft linens, smart TV, ample storage, and ceiling fans for added comfort.brbr★ BathroomsbrEn-Suite (Primary): with a double vanity, walk-in glass shower, and modern tile.brSecond Bathroom: Full bath with a deep soaking tub, perfect after a beach day.brBoth are stocked with towels, hair dryers, and travel-size essentials to start you off.brbr★ Outdoor/PoolbrYour private tropical escape features an in-ground saltwater pool with evening lighting, a mini putting green, and a fully fenced backyard for complete privacy. Enjoy al fresco dining, sunbathing, or just lounging in this serene outdoor oasis.Please note that pool temperature may vary depending on outdoor conditions, and during colder weather, it may not always reach the desired setting.brPool heated with an additional fee of $50/day, upon request from Nov 1st to April 30th. Pool heated at 86F from 8am to 4pm. brbr★ LocationbrSituated in Sarasota’s charming Sunnyside Park neighborhood, this home is ideally located. You’ll have easy access to top restaurants, shopping, entertainment —all while enjoying a peaceful residential setting.brDowntown Sarasota: 7 min drivebrSiesta Key Beach: 12 min drivebrLido Key/St Armands Circle: 15 min drivebrSarasota Airport: 15 min drivebrbr★ LaundrybrIn-unit washer and dryer available for guest use. Located discreetly within the home for easy mid-trip laundry or post-beach cleanup.brbr★ Parkingbrone-car garage is reserved for the owner. 2 spaces available on the driveway. brbr★ House Rules:br- 7-night minimum staybr- No pets, parties, or smokingbr- AC must remain above 70°F and heat below 77°Fbr- Keep doors/windows closed with HVAC runningbr- Pool use is at your own risk—children must be supervised at all times.brbr★Add-on:brTraveling with a little one We offer a Pack 'n Play for use during your stay for a one-time fee of $50. This includes clean, fitted sheets for your convenience. Just let us know in advance if you'd like to add this to your booking!brbr★ Wildlife Awareness:brPlease enjoy Florida’s diverse wildlife respectfully and safely. Learn more at the Florida Fish and Wildlife Conservation Commission.brbrYour Sarasota escape begins here—book today for the perfect blend of sunshine, style, and sophistication! brVR25-00122
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(52)

$337.65

/ Nightly
Private Vacation Home

Sarasota Waterfront Paradise- Location, Location...!!

Sarasota, Florida, United States

Welcome to your private waterfront paradise in the heart of Sarasota! This beautifully designed 3-bedroom, 2-bathroom retreat offers the perfect blend of luxury, comfort, and serene natural surroundings. With a heated pool and spa, this home is fully stocked to provide you with the ultimate indoor-outdoor vacation experience. Just added...new floating dock, great for launching the kayaks!brbrNestled in the upscale Southgate neighborhood, this charming property is just minutes from the world-renowned Siesta Key Beach, Longboat Key, St. Armand's Circle, and downtown Sarasota. Set along the tranquil Philippi River, which flows into the stunning Sarasota Bay, you'll enjoy breathtaking water views and an abundance of nature at your doorstep.brbrStep inside this one-level home and be greeted by an open, inviting layout. The modern kitchen is fully equipped and features a sleek design that flows seamlessly into the dining and living areas. Whether you're preparing a gourmet meal or relaxing in the living room, you’ll be treated to peaceful views of the lush backyard and riverfront. The home’s Feng Shui promotes harmony and balance, enhancing the indoor-outdoor connection.brbrThe spacious master suite offers a luxurious retreat, complete with a private, newly remodeled bathroom, a walk-in closet, designer furnishings, and a plush king-size bed. Unwind and enjoy your favorite shows on the flat-screen TV in this peaceful haven. The second bedroom features a queen-size bed, flat screen TV, and upscale furnishings, while the third bedroom is perfect for kids or friends, with two single beds. These two bedrooms share a fully remodeled bathroom, designed with a stylish, modern coastal vibe.brbrBeyond the interior, the property truly shines with its outdoor spaces. Enjoy sunny days on the expansive deck, cook up a delicious meal on the grill, or unwind around the firepit with spectacular views of the river. The private backyard is perfect for lounging or exploring, and nature lovers will delight in the chance to pick fresh mangoes from the trees. We also provide kayaks, bicycles, beach chairs, pool toys, and everything you need for a day of adventure on the water or the beach.brbrFor your convenience, the home features an attached garage with a washer and dryer, as well as beautiful new epoxy flooring. The pool and spa area has been recently resurfaced with Pebble-Tec and is equipped with a digital temperature control system, ensuring year-round comfort.brbrOne of the standout features of this home is its seamless transition from indoor to outdoor living. The spacious meditation room opens up to the pool and spa area, offering a tranquil space to relax and enjoy the views of the flowing river. From here, you can continue to the private deck or take a stroll through the lush grass yard to the firepit. Whether you're relaxing by the pool, kayaking on the river, or enjoying a barbecue with family and friends, this home offers the perfect setting to unwind and make lasting memories.brbrBook your stay today and experience the best of Sarasota living, where comfort, beauty, and nature meet at this one-of-a-kind waterfront retreat.
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
Slider Thumb

$400.0

/ Nightly
Private Vacation Home

Charming 3BR/2BA Pool Home in Sarasota, Total Comfort, Minutes to Siesta Key!

Sarasota, Florida, United States

Relax in this enchanting, fully renovated pool home in Sarasota’s Forest Lakes community—just 15 minutes from Siesta Key Beach. AVAILABLE for 30-DAY MINIMUM STAYS with 1–3–6–9-month options. This furnished 3-bed, 2-bath retreat sleeps 8 and offers a bright open layout, porcelain tile floors, vaulted ceilings, and a modern kitchen with stainless-steel appliances, granite counters, and a functional island. The spacious primary suite includes custom walk-in closets and a spa-like bathroom with dual vanities and dual rain shower heads. Enjoy seamless indoor-outdoor living with sliding doors leading to the private fenced yard and sparkling pool—perfect for relaxing or entertaining. Stay comfortable with central A/C, heating, and thoughtful amenities like hair dryers, Wi-Fi, and in-garage laundry. Rent includes WIFI, electricity, water, lawn care, pest control, and pool maintenance.
Bed 3

Bed

Bath 2

Bath

Sleep 30

Sleeps
Slider Thumb
Exceptional(3)

$200.06

/ Nightly
Apartment

Rustic Beach Hideaway

Sarasota, Florida, United States

Welcome to your cozy Siesta Key retreat, just steps from the pristine white sands of Crescent Beach. This charming one-bedroom apartment is the perfect getaway for couples or solo travelers looking for a peaceful escape with a touch of rustic charm. Enjoy your morning coffee in the private garden or gather around the fire pit in the evening for a cozy, starlit experience, this outdoor space is perfect for relaxing after a day at the beach.
Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
Slider Thumb
Exceptional(26)

$267.5

/ Nightly
Private Vacation Home

Private Swim Spa-Lanai | 3BR Near Siesta Key | Coastal Getaway | Sleeps10

Sarasota, Florida, United States

Welcome to Anchors Away! This three-bedroom, two-bath home with Swim Spa will not disappoint those who like to get away and relax.brbrOnce you enter the home, you are greeted by a large family living space with lots of comfortable seating and a large SMART flat-screen TV for you and your guests to enjoy your favorite programs. The family room opens up to the dining room which sits 10 comfortably. Right off the dining room is access to both the lanai and the carport.brbrThe large, spacious kitchen offers lots of cabinets and countertops for preparing meals effortlessly. The farmhouse sink, extra storage, and prepping area make it enjoyable to prep for meals. It is very accessible to the dining area for ease of serving.brbrThe primary bedroom is located off the kitchen and offers sleeping for 4 with a king-sized bed and a double day bed. The ensuite bathroom boasts a beautiful tiled walk-in shower. The second bedroom sleeps two with a Queen bed and a TV to enjoy. The third bedroom has a king-sized bed as well as a TV. The second bathroom has a tub/shower combo. There is also a rollaway bed available for extra sleeping needs. brbrOnce you exit the home to the backyard oasis, you may never want to leave. You will step into the screened lanai porch that has a comfortable sectional and flat-screen TV for extra entertainment. Beyond the lanai is a new beautiful Swim Spa, loungers and more seating for enjoying the beautiful Florida weather. brbrSwim Spas represent a hybrid of a spa (heated and hydro-massage features) and a pool (with its size to allow for more people to enjoy it and enough space to facilitate a versatile range of low-impact exercises) providing a complete system for swimming, exercise, and relaxation. Designed specifically for producing resistance, jets or a propulsion system create the perfect environment for swimming or performing general aerobics and light exercise activities. It's also these propulsion systems that create the continuous current that allows people to swim-in-place for the most effective swimming workouts and experience possible, eliminating the flip-turn stops after a few short strokes that is a common drawback with a traditional swimming pool experience.brbrIf you do decide to venture out, you couldn't choose a better location. It is within walking and short driving distance of some of the best dining and shopping choices in Sarasota. It is also only a 10-minute drive to Walt's Fish Market, the only market/restaurant in Sarasota that sells fish and seafood caught the same day you buy it!brbrAnd of course, you are just a short drive to the beautiful beaches of Siesta Key which has been named over and over as one of the best beaches in the world with beautiful quartz sand. Siesta Key Village has great shops, restaurants and nightlife.brbr*This is a family home nestled in a quiet neighborhood. Weekly pool and lawn care will happen during your stay.brbr*PET OWNERS: This property is dog friendly for one dog with a maximum weight of 25 pounds and a non-refundable pet fee of $150 for the first week. There is a $50 fee per week for any additional weeks booked. Also, certain breeds are excluded. You must check with our office prior to your trip for details on weight and breed limitations.brbrOur Cancellation Policy: To protect our owners from loss of income, ALL MONIES PAID TOWARDS YOUR RESERVATION MAY BE NON-REFUNDABLE AFTER A CERTAIN DATE! FULL AND PARTIAL REFUNDS MAY BE GIVEN UNDER CERTAIN CONDITIONS. Ask our office for details, or check your rental agreement.
Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
Slider Thumb
Exceptional(1)

$254.61

/ Nightly
Private Vacation Home

Beautiful Pool Home Close to Top Beaches and Golf!

Sarasota, Florida, United States

Welcome to Mauna Loa Hideaway in gorgeous Sarasota, Florida! This stunning 3-bedroom, 3-bathroom home with private backyard and screened-in pool has been beautifully updated and is the perfect getaway for families or groups of friends looking for a comfortable and convenient home from which to explore this amazing gulf side city. brbrJust a short drive to Siesta Key Beach, Lido Key Beach, Sarasota Jungle Gardens, Myakka State Park, University Town Center (UTC) Mall, local golf courses and other great Sarasota attractions and amenities!brbr- Private screened-in pool and patio areabr- Quiet Sarasota neighborhood br- Outdoor seating and dining areasbr- Outdoor grill area for family cookoutsbr- Beautifully updated interior br- Fully equipped kitchen br- Spacious primary suite with king bed and ensuite bathroombr- Family-friendly layout with bunk room and trundle bedbr- Dedicated office/workspace for remote workbr- Washer and dryer br- Perfect for families, groups, beach trips, golf getaways, and long staysbr- Convenient location close to top beaches, parks, shopping, dining, and attractionsbr brAs soon as you step inside, you'll be greeted by a beautifully decorated interior that features high-end furnishings and all the modern amenities you need for a comfortable stay. The spacious living room is the perfect place to relax and unwind after a day at the beach, featuring a large white sectional sofa, a flat-screen TV, and a cozy fireplace that's perfect for cooler nights.brbrThe dining room features a cute dinette that's perfect for enjoying meals with your loved ones, while the fully equipped kitchen boasts granite countertops, wood cabinetry, and stainless-steel appliances. Whether you're a seasoned chef or just looking to whip up some quick and easy meals, you'll love cooking and entertaining in this beautiful space.brbrThe primary bedroom is a true oasis of comfort and luxury, featuring a king-size bed, an ensuite bathroom with a large walk-in shower, and a spacious walk-in closet that's perfect for storing your clothes and belongings. The second bedroom features a full-size bed, nightstands, and plenty of closet space, while the third bedroom is perfect for kids, featuring a bunk bed with a trundle and an office space that's perfect for getting work done on the go. There is also an ensuite bathroom with a walk-in shower. brbrThe 3rd bathroom offers a tub and shower to make bathing the kids after the beach a breeze. brbrBut the real highlight of this stunning vacation home is the private screened-in pool area. Surrounded by lush landscaping and featuring plenty of comfortable loungers and outdoor table, this is the perfect spot to relax and soak up the Florida sunshine. Take a dip in the sparkling pool, enjoy a cold drink and some good conversation, or simply kick back and enjoy the peace and tranquility of your own private oasis.brbrWhen you're ready to venture out and explore, you'll find that this rental house is conveniently located just a 15-minute drive to the famous Siesta Key beach.  Some of Sarasota's best parks, and attractions are just a short drive away, and there are plenty of other beautiful beaches within easy reach. You'll also find plenty of great restaurants, bars, and shops nearby, as well as attractions like the Ringling Museum of Art and the Marie Selby Botanical Gardens.brbrAdditional amenities in this beautiful vacation home include a washer and dryer, so you can pack light and stay fresh throughout your stay. Whether you're looking for a relaxing getaway or an action-packed adventure, this stunning vacation home in Sarasota, Florida is the perfect choice for your next getaway. Book your stay today and start counting down the days until you can enjoy all the sun, sand, and fun that this amazing city has to offer!brbrTop Beachesbr----------------------------br- Siesta Key Beach – Approx. 15 minutes with world-famous white quartz sand crystal-clear Gulf waters, beach volleyball, sunsets, restaurants, and nightlifebr - Lido Beach – Approx. 15 minutes with relaxing beach atmosphere close to shopping and dining at St. Armands Circlebr- South Lido Park – Approx. 18 minutes with nature trails, kayaking, picnic areas, and quieter beach accessbr- Longboat Key Beach – Approx. 20 minutes with peaceful Gulf beaches and scenic coastal viewsbr- Turtle Beach – Approx. 20 minutes, great for kayaking, shelling, and boatingbrbrTop Attractions Within 10–15 Minutesbr----------------------------br- Sarasota Jungle Gardens: Family-friendly attraction with flamingos, tropical gardens, and wildlifebr- The John and Mable Ringling Museum of Art: Sarasota’s iconic museum and historic estatebr- Marie Selby Botanical Gardens: Stunning waterfront botanical gardens and butterfly displaysbr- St. Armands Circle: Upscale shopping, dining, cafes, and nightlifebr- University Town Center (UTC) Mall: Luxury shopping, restaurants, and entertainmentbr- Nathan Benderson Park: Walking trails, rowing events, kayaking, and outdoor recreationbr- Myakka River State Park: Hiking, wildlife viewing, airboat tours, and Old Florida scenerybr- Mote Marine Laboratory & Aquarium: Marine exhibits, sharks, sea turtles, and family activitiesbr- Bayfront Park: Waterfront views, marina, playground, and sunset walksbrbrNearby Golf Coursesbr----------------------------brThe Meadows Country ClubbrBobby Jones Golf ClubbrUniversity Park Country ClubbrbrClosest Airportsbr----------------------------brSarasota-Bradenton International Airport – Approx. 15 minutesbrSt. Pete–Clearwater International Airport – Approx. 1 hourbrTampa International Airport – Approx. 1 hour 15 minutesbrbrbrbrWelcome to Sarasota!br----------------------------brConsidered one of the top places to visit in Florida, Sarasota is home to white sandy beaches, crystal clear waters from the Gulf and a diverse community full of enriching arts and culture.brbrThe Sarasota beaches are comprised of six islands, each with their own unique personality, natural beauty, and fun adventures. Longboat Key is the northernmost key with 12 miles of sandy shores and a place sea turtles come to nest. Lido Key has three beaches and home to the famed St. Armand’s Circle. Siesta Key has two main bridges and is regarded as the #1 beach in the world. Caspersen Beach in Venice is dog-friendly and the perfect place for shark tooth hunters. Manasota Key is the nature lovers dream with walking trails from Gulf to bay. And finally, Casey Key has an 18-acre park, picnic areas and concession stand, perfect for a fun day trip.brbrAfter a day enjoying one of the many beaches, explore another side of Sarasota- the arts, restaurants, and nightlife. Known as Florida’s Cultural Coast, Sarasota County has an array of museums, galleries and performing art venues.brbrFor the foodie in all of us, enjoy several award-winning restaurants with views of the Gulf, skyline and more. From fine dining to small seafood joints and numerous food festivals, there is an abundance of choices.
Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps

Home Rent a place that suits your needs

Condo

Condo

View 1177 Condo
Cottage

Cottage

View 58 Cottage
Private vacation home

Private vacation home

View 1474 Private vacation home
Villa

Villa

View 145 Villa

Home Most popular vacation rentals in Sarasota

Slider Thumb
Exceptional(1)

$1972.73

/ Nightly
Private vacation home

Luxury Villa • Waterfront 9BR/9BA • Pool + Spa • Steps to Lido Key Beach

Sarasota, Florida, United States

Bed 9

Bed

Bath 9

Bath

Sleep 10

Sleeps
Slider Thumb
Exceptional(1)

$1981.32

/ Nightly
Private vacation home

Shore is Something | 5000sqft, Walk to Lido Beach, Bike to St Armand Circle

Sarasota, Florida, United States

Bed 10

Bed

Bath 11

Bath

Sleep 12

Sleeps
Slider Thumb
Exceptional(1)

$2014.81

/ Nightly
Private vacation home

Siesta Beachfront Paradise: Infinity Pool & Spa!

Sarasota, Florida, United States

Bed 8

Bed

Bath 9

Bath

Sleep 22

Sleeps
Slider Thumb
Exceptional(1)

$2070.75

/ Nightly
Private vacation home

Steps to Beach/Pool w/Slide and Chipping Green

Sarasota, Florida, United States

Bed 8

Bed

Bath 8

Bath

Sleep 19

Sleeps
Slider Thumb
Exceptional(1)

$2113.04

/ Nightly
Private vacation home

Lagoon Pool/Slide/Spa - Beach Volleyball/Ping Pong

Sarasota, Florida, United States

Bed 7

Bed

Bath 8

Bath

Sleep 19

Sleeps
Slider Thumb
Exceptional(1)

$2113.99

/ Nightly
Private vacation home

Holiday Home 'Modern Townhouse with Stunning View' with Sea View, Wi-Fi and Air Conditioning

Fuengirola, Andalusia, Spain

Bed 5

Bed

Bath 5

Bath

Sleep 12

Sleeps
Slider Thumb
Exceptional(1)

$2137.71

/ Nightly
Private vacation home

#1 Rooftop Gulf Views-Theatre Room-Unmatched Slide

Sarasota, Florida, United States

Bed 5

Bed

Bath 6

Bath

Sleep 16

Sleeps
Slider Thumb
Exceptional(1)

$2211.43

/ Nightly
Private vacation home

Sport Court Feat. Pickleball - Theatre Room - Pool

Sarasota, Florida, United States

Bed 7

Bed

Bath 8

Bath

Sleep 19

Sleeps
Slider Thumb
Exceptional(1)

$2292.60

/ Nightly
Private vacation home

60ft Water Slide/Spa-Theatre Room/Air Hockey

Sarasota, Florida, United States

Bed 7

Bed

Bath 7

Bath

Sleep 18

Sleeps
Slider Thumb
Exceptional(1)

$2461.78

/ Nightly
Private vacation home

Pirate House: Gulf Front, Pool, #1 Location Lido Key, St. Armands One Block.

Sarasota, Florida, United States

Bed 5

Bed

Bath 5

Bath

Sleep 10

Sleeps

Most Popular Cities in Florida